Under the Gun
by Annaleise Marie
Summary: [Revamp/Expansion of "Playing for Keeps"] Dean's a professional kidnapper, stealing and then returning the children of the elite rich for ridiculous amounts of money. When his current job went sideways, he figured that he would wind up in jail, dragging down everything and everyone he loved with him. He never expected what actually happened. And he never expected what came next.
1. Good Samaritan

**Under the Gun**  
Annaleise Marie  
 _cross-posted from livejournal  
_ _username: girlgotagun_

 **Pairing(s)** : Dean/Cas  
 **Full List of Kinks** : first time, virginity, hurt/comfort, schmoop/WAFF, anal, rimming, fingering, oral, praise, sexual tension, masturbation, angst  
 **WARNING** : Graphic retrospective descriptions of child abuse (non-sexual).

This story is a revamp and continuation of a smaller fill, "Playing for Keeps". You can check that one out if you want, for a little bit of an idea of what to expect from this story. There was a lot that I wanted to do with this prompt, though, that I couldn't in my self-imposed fill limit, so this version will be _much_ more in-depth, much more carefully planned out, and it will go beyond the end point of PFK. Think of it as Playing for Keeps: Redeux. I hope you guys enjoy it! 3

 **Chapter One** : Good Samaritan

X

 _"Yeah she's got a criminal mind  
He's got a reason to pray  
His life is under the gun  
He's got to hold every day _

_Now he just wants to wake up  
Yeah, just to prove it's a dream  
Cause she's an angel for sure  
But that remains to be seen _

_Because heaven sends and heaven takes  
Crashing cars in his brain  
Keep him tied up to a dream  
And only she can set him free…"_

—The Killers, "Under the Gun"

X

Sam went to school every weekday from seven-thirty in the morning until two-thirty in the afternoon. It was, in Dean's opinion, a complete waste of seven perfectly good hours of daylight. He himself had dropped out at seventeen and gotten his GED. No one gave a damn if he had filled a chair that last year, as long as he could rebuild an engine and change some oil. He and Sam were both lined up to take over Singer & Winchester Automotive Repair, the business that their father and Uncle Bobby had built from the ground up.

But Sam seemed determined to finish school. The kid was just a month shy of eighteen, but apparently he still hadn't given up on his dream of going on to college, becoming a lawyer.

John had laughed when Sam first mentioned it. "Don't need a lawyer as long as we do our jobs right." That was probably the nicest thing he had said in reply to Sam voicing his desire to do anything other than take over the garage.

As for Dean, he was okay with it. He liked cars, liked working with his dad and Bobby, liked helping to build something without the pressure of bringing it into existence from nothing. The shop was a lot like Sam—his dad had helped create it, had tenuously gotten it through its first year, and as Dean got older more and more of the responsibility for its well-being was handed over to him. And Dean was okay with that, too.

Sam wanted no part in it. He wasn't much for mechanics, for hands-on work. He liked to work with his mind. Dean figured there was nothing wrong with that; the world needed all sorts, and Sammy was smart as hell. Dean didn't have a problem with Sam's plan, really. The shop was located just outside Palo Alto, anyway, so he figured even if Sam wanted to chase the ivy, he wouldn't end up too far away.

So Dean didn't have it in him to tell Sam it was useless, that Dad would never go for it, that Sam might as well follow in Dean's footsteps and drop out. Get his GED and trade in his nice clean polo shirts for grease-stained henleys and split knuckles. He just kept driving to the high school every day and waiting at the curb for the final bell to ring, waiting to take Sammy home.

It was a Friday—Dean remembered because the fight between Sam and their dad happened the next morning, and Dean wished for once that Sam was in school instead of at the shop—and Dean was leaning against the Impala, the collar of his dad's old leather jacket turned up against the sharp February air. It didn't get very cold in their part of California, but when a storm brewed out at sea cold Pacific winds were pushed inland, and the air had a bite to it. He would've sat in the Impala as he waited, but for all of the damage that he and Sammy had done to the car over the years—the initials carved in the dash, the legos in the heating vents—John had finally put his foot down when it came to Dean smoking in it.

"You want to destroy your lungs, whatever—you're not destroying the car." Yeah. That was John Winchester.

So it was a Friday, and Dean was leaning against the Impala as he waited for the bell to ring, for Sam to come hurrying down the wide stone steps on graceless coltish legs. The kid could've been popular—he was well-liked enough—but he never stayed to socialize. Dean didn't get why; that had been the only part of high school he liked.

He looked around when he heard a high-pitched whining sound, eyes scanning the sidewalk stretching out to either side of him, and then the street. His first thought was that it was an injured animal. But when he saw nothing of the kind he stood up, letting his cigarette fall to the ground as he waited for the sound again. It was a couple of seconds, and then the whimper ripped through the air again. He took a few steps, searching around for the source. He moved toward it every time it rang out, and searched when it stopped.

Finally, he came to the playground across the street, and then to the large jungle gym. It was under the slide that he found the source of the noise, and when he did he was shocked by what he was seeing. The sound was coming from a little girl, crouched in the dirt. Her long blonde hair was matted, stuck to her face by trails of tears and snot. Every inch of her was covered in dirt, as though she had been crawling around under the jungle gym for days. Leaves and twigs were stuck to her, and she was shivering in a short-sleeved shirt, no jacket in sight.

"Hey, kid." Dean tried to keep his voice calm and quiet, tried not to startle the girl. "What're you doing out here? Where are your parents?"

The girl shook her head, a sob escaping her throat. Dean shrugged off his jacket and covered her with it, sighing inwardly as the girl wiped her running nose on the collar. Can't machine wash leather. Great.

"Are you lost? Where do you live?" Dean looked around, hoping to spot some adults who looked like they were missing a kid. There was no one around. And he figured that made sense—by the looks of the girl, she had been away from her family for awhile. He reached into the pocket of his jacket, his movements slow and smooth so that the girl didn't panic, and took out his cell phone. "Do you know your phone number?" The girl shook her head, a wail rising in her throat. "Okay, okay. That's okay, kid." Dean frowned, unsure of what else he could do.

He thought of dialing 411. It was worth a shot. "Okay, what's your name?"

"E-Emily," the girl whimpered.

Dean exhaled. Okay, that was something. "Okay, Emily. I'm Dean."

"De'n," the girl repeated, sniffling. She sounded so much like Sam as a kid that Dean nearly laughed.

"Right. So Emily, can you tell me what your mommy and daddy's names are?" Now that the girl was talking, wasn't crying as hard, Dean was hopeful.

The girl looked confused. "My mommy is Mama. Daddy is Papa."

Dean sighed. "Yeah, okay but… Your name's Emily, right? You're their daughter and you're Emily. So they're your parents and they're…" He waited for her to fill in the blank.

"Mommy and Daddy."

Okay. So that was going nowhere. Dean looked around again, trying to decide what to do.

Finally he sighed, only able to think of one thing. "Okay, Emily. Come with me; I'll take you to the police station. Maybe they can find you."

The little girl nodded and took Dean's offered hand as she stood up and walked with him to the Impala.

Dean was sure that anyone who saw her climb into his car would think that he was kidnapping her.

X

Turning a lost kid in to the police is hard. Especially when that kid is Emily Brewer. It turned out Emily was four years old. She was the youngest daughter of Ned and Stacey Brewer. Her older sister, Jenny, went to school with Sam. Emily had gone missing the day before, administration at her elementary school confirming that she had boarded her bus in the afternoon, but never arriving home. The best guess that anyone had as to why she was hiding out in the playground was that she had recognized her sister's school but when she was unable to find her she got scared and hid.

Whatever. Dean was just glad the kid was safe.

The police, however, were reluctant to leave it at that. So Dean was questioned five separate times by three different officers about how he wound up bringing Jenny in. It was a little ridiculous—why would he return a kid if he had snatched her in the first place?

Eventually, though, his story checked out to their satisfaction, and he was allowed to leave. He checked his watch. Sam's last class had let out an hour ago. He was going to be in full bitch-mode by the time Dean got there.

His hand had just landed on the main door of the station when a woman's voice called out his name. He turned to see a man and woman who appeared to be about his dad's age, their faces weary and exhausted with the remnants of fear and sorrow. The woman was holding Emily. The girl's face had been cleaned up but she was still a mess, and Dean suddenly remembered the snot that she had wiped on his jacket, which he had put back on without thinking. Awesome.

"You're Dean Winchester, right?" the woman, who Dean guessed was Stacey Brewer, asked. "You're the man who found our daughter?"

Dean nodded. "Uh, yeah. I was just waiting to pick up my brother from school and I found her. No big deal."

"It's a very big deal." Ned Brewer said gravely, wrapping his arm around his wife. "We were so worried that… Well, we're so relieved to have her back. We can't thank you enough."

He stepped forward and held his hand out. Dean thought that he wanted to shake hands, but when he moved to grab the man's hand he felt a piece of paper being pressed into his palm.

"Thank you so much," Stacey said, her eyes welling up.

Dean shifted uncomfortably. "No worries. You guys have a good one." He smiled at the little girl. "Bye, Emily."

"Bye, De'n."

X

Dean didn't look at the slip of paper that Ned had pressed into his hand until he was back in the Impala, and when he did he nearly had a heart attack. It was a check for five thousand dollars. _Five thousand dollars_. The Brewers had paid him five thousand dollars for essentially giving their kid a ride to the police station. Something that any decent person would do. It was more than he made two months at the shop.

He eyed the address and phone number at the top of the check. He should return it. He hadn't done anything to deserve that kind of money.

But then again, he hadn't asked them for it… It wasn't like he had ransomed the kid. And it was a lot of money—there was a lot he could do with it.

He slipped the check into his pocket.

X

Dean walked into the kitchen on Saturday morning, rubbing his eyes to rid the last of the blur of sleep as he scratched his stomach under the hem of his shirt. Sam was already at the table, the newspaper spread out in front of him as he scanned the front page, a half-eaten bowl of cereal and cup of coffee sitting forgotten to the side.

"Mornin', Sammy." The words were spoken through a yawn as Dean rummaged through the cabinet for a coffee mug.

Sam didn't answer him, and once Dean had poured himself a nice, strong cup of coffee he turned, leaning against the counter as he raised an eyebrow at his little brother. "Still not talking to me? Or has something else got you acting all sunshine-y this fine morning?"

Sam didn't look up from the newspaper. "Jerk."

"Bitch."

Sam rolled his eyes but gave no indication that he was going to continue the conversation—civil or not. He had been royally pissed off when Dean had finally gotten to the school to pick him up. Apparently some cheerleader named Rachel Nave had cornered him as he waited for Dean and asked him to prom. Dean hadn't seen what was so bad about that.

Sam had sighed and rolled his eyes. "She doesn't even like me, Dean. She just wants to go with me to get to you."

Dean was sure that wasn't it… Never mind if he would be proven wrong two months later when she had tiptoed from Sammy's room, wearing only his brother's tux shirt, and slipped into bed with Dean, whispering all manner of filthy things until he finally pulled her onto his lap and let her ride him hard. She screamed when she came, waking up Sam. His little brother hadn't looked surprised. Dean had told him that hey, at least he had gotten laid too. That hadn't helped any, really. Dean had given her a ride home and Sam never brought another girl to the house.

And it was like Sam could see the future, because after Dean had tried to tell him that there was no way a girl was doing that Sam had gone silent and hadn't spoken to Dean since.

The silence in the kitchen was interrupted when the sound of the mail slot rattled. Sam was out of his seat like a shot, hurrying to pick up the mail and flip through the envelopes.

"Jeez, Sammy, you expecting a ticket out of here or something?"

Dean didn't know how right he was.

X

"You're not going! I'm not going to tell you again!"

"I don't need your permission! I'm going to be eighteen; I'll be an adult. You can't keep me here!"

"Yeah, hotshot? How're you going to pay for it? You're still a kid, Sam, and we need you here! Not traipsing off to school and abandoning the family!"

"I got a full ride!"

"For tuition! How're you going to live?"

There was a beat of silence as Sam and John squared off, Sam turning the question over in his head, floundering for an answer. A muscle twitched in his jaw and Dean was struck by how much the two men were alike; probably why they never got along. The Winchester men were full of a certain amount of self-loathing; couldn't stand to see themselves in other people.

"I'll figure it out." Sam's voice was hard, determined. "But I'm going, and you can't stop me."

Dean eyed the letter on the coffee table. The letter with the Stanford Office of Admissions logo. The letter that had torn it all down. He sighed as his dad and brother started yelling again.

Sam was right; the kid had to get out of here. This place was killing him. And if their dad wouldn't help him, it wouldn't stop him. Sammy was gonna go one way or another. But John was also right; Sam had no idea what it was going to take. Dean knew that their dad wouldn't let Sam live there and go to college; working at the shop would be required if he was going to live at home as an adult. So there'd be room and board. Meal plans. Books and lab fees. A hundred little things that came with going off to college.

He thought of the check that he had tucked into his dresser drawer alongside mismatched socks and boxer briefs. While Sam and their dad yelled, he slid the letter across the table, the number for the office of admissions printed under the emblem, and pocketed that, too.

X

Dean had met Charlie Bradbury back in high school; back before he dropped out and before she went on the run. The truly genius part about Charlie when she ran was that she hadn't gone anywhere. She was an expert hacker—which was actually what got her in trouble in the first place—and she turned her own downfall on the cops, laying a paper trail all the way across the country. Her passport was recorded at customs leaving America and then again in the Czech Republic. As far as either of them knew, the FBI was still looking for her somewhere around Ostrava.

In reality, she had become a hermit, rarely leaving the house she rented in the outskirts of Palo Alto. The house was rented under some bogus identity, the rent wired to a landlord who believed that she had severe agoraphobia. In the beginning the man had done some routine inspections, but after a few months he seemed to come to the conclusion that she wasn't going to trash the place and mostly left her alone as long as the grass didn't get too high and the rent money came on time. Charlie ran a small-time credit card scheme, creating fake apps that never worked _quite_ right but were hard to delete and rang up small in-app purchases. A few hundred downloads a month and she had made rent and grocery money, all siphoned in small enough amounts that no one ever challenged them. She lived a simple life, and Dean liked that.

Once a week he went to Walmart and picked up an order that she had placed online for groceries and personal items and brought them to her. That week, he brought her order, as well as the cards he had bought with the cashed check and the Stanford letter.

The door opened shortly after he rung the bell, and he stepped inside. "Hey Charlie. I need a favor." That was how they were; straight-forward and simple. Dean liked that too.

He helped her put the groceries away as he explained the situation to her. About the missing girl, the check, the Stanford letter, the fight, Sammy.

"Okay." Charlie shuffled through the cards. Five of them. They had a limit of a thousand dollars each. "So what are you wanting me to do?"

Dean finished putting the last of the groceries away and grabbed a couple of beers from the fridge before sitting down. He popped the tops and handed one to Charlie. "Sam can't come up with that much money in time. Not without sacrificing his last semester, and if he does that, he risks them yanking back his acceptance. And I mean, I don't want him to go through with it, because it's gonna destroy the last of the family we've got. But if he's gonna do it anyway—which he is—I don't wanna watch him fail trying to juggle it all."

He took a drink of his beer as Charlie nodded before he continued. "Problem is, Dad's got Sam's pride all up. He's not gonna take any help from me. So I need you to make it look like he got a scholarship or grant or something."

Charlie winced. "Dean, I get what you're trying to do but… I mean, this isn't even really enough for a semester. Even without tuition. I mean, _maybe_ it would cover the dorm and meal plan. But lab fees and books…" She trailed off. "I can do it; of course I'll do it. But I'm just sort of thinking you're fighting a losing battle here."

Dean sighed. "Okay, so what, that leaves like five hundred for books and a couple hundred for lab fees?" He was guessing, based on what he had seen scrawled in the notebook on Sam's desk. "I can figure that out, scrape it out of what I get paid at the shop. Just do what you can, okay?"

Charlie nodded. "If you're sure. It'll take a few days. I can do a rush job, but if I've got the time to wait out the security periods rather than working around them I'm way less likely to be detected."

"That's fine." Dean took another drink, the pressure in his chest lessening now that he knew the whole plan was in motion. "Thanks."

"You wanna thank me, you handle the admissions office. I hate talking to people on the phone."

"Deal."


	2. Fairy Tales

**Under the Gun**  
Annaleise Marie  
 _cross-posted from livejournal  
_ _username: girlgotagun_

 **Chapter Two** : Fairy Tales

 **AN** : It seems worth mentioning that in this version of the story, Cas and Dean will not actually meet as soon. I mean, they'll meet in the same point in the story as before, but there will be a few chapters before we get there, since we're delving deeper into the background. Hopefully you guys will enjoy it all the same. :) Also, fun fact: I didn't realize when I started this story that, because Cas is six years younger than Dean in this story, he would be sixteen at the time that the first installment of Dean's history. So buckle up for some high school Cas!

X

Castiel Novak paused on the front steps of the family estate, his stomach clenching at the thought of going in. He didn't enjoy school—he was a small kid, the smallest boy in the sophomore class at his high school, and so he was an easy target for bullies. But the misery that the idea of going to school filled him with was nothing compared to the hollowed-out feeling that settled in his gut when he had to go home. It had always been hard there, his father's tyrannic reign making life around the large house nearly unbearable, but it had become truly horrific in the last two years. Ever since that night…

He pushed the memory from his head and swallowed around the lump in his throat. He missed Anna. The sweet-tempered woman who had served as his nanny, filling in as a tenuous mother replacement for each of the Novak boys after their real mother had passed away, had stood here with him, patient as he refused to go in. There was a story that she told him as they stood there.

 _"There once was a house that sat near the sea. The wind whipped cold over the grounds and bit at the flowers that would barely bloom in the poisoned dirt. In the furthest room of the top floor there lived a little prince, imprisoned by a large and terrible monster. The little prince was sweet and kind, but he was very afraid of the monster, and he waited for someone to come and slay it, freeing him from his prison. But all who tried failed…"_

Castiel couldn't remember now how the story ended. He couldn't even remember if it had a real ending, or if it was a happy one. He hadn't understood the parallels as a child. He knew he was the prince in the story—or maybe it was each of the Novaks who had been under Anna's care since she was only twenty—but that was all.

Anna had tried to free him. Anna had stood up to their father.

Anna lasted a year after that before she broke, and even her loyalty to Castiel and his brothers couldn't keep her there. She quit; fled the house by the sea with the biting winds and the poisoned dirt.

Castiel was pretty sure by this point that the story had no end. He would be locked in his prison forever.

The monster was too strong, and too cunning.

The house was quiet when he finally got up the nerve to go inside, but instead of bringing him a sense of relief, it quickened his pulse. Yelling and anger was predictable. The quiet simmer was dangerous. He paused just outside of the doorway to his father's office, listening for movement as he lingered out of sight. He could hear the sound of the man typing on his computer, then a pause as the sound of ice clinking around in a glass reached his ears. His eyes fell closed and his shoulders hunched. It was going to be one of those weekends.

He stepped back, circling around the entrance hall and slipping through the doorway of the sitting room, taking the long way through the kitchen to the back stairs to avoid passing by the office door. His footsteps were nearly silent on the stairs, years of attempts at moving quietly, going unnoticed assisting in the feat as he hurried up to the third floor.

He stepped out into the hallway and nearly slammed into his older brother, Luc. He had forgotten that the eldest Novak was going to be home from college for the weekend. His father always had a reason to drink; this weekend it was probably Luc.

"Hey, Cassie." The young man gave him a lopsided grin. "Sneaking around again?"

"I don't enjoy baiting our father." Castiel's tone made the unspoken _unlike you_ clear.

Luc shrugged easily. "Can't be afraid of him forever, little brother."

"Can't we?" Castiel didn't understand his oldest brother's lack of concern. After all they had been through, all they had seen, how could Luc act so unaffected? Michael, the second-oldest, made more sense—he may be their father's pet, the most obedient and worshipping of the brothers, but at least it came from years of being beaten down until he was molded into what he was. It was understandable. Luc's indifference was not.

"What more can he do to us? What can he take that he hasn't taken yet?"

It was the question that haunted Castiel's every waking thought, as well as most of his dreams.

X

The shouting started at a little after eight that night, Luc and his father's angry voices floating up through the floor. Judging by the direction, they had likely run into each other on the second-floor landing. Castiel tried not to listen; the exact words were indistinct. When he had been younger, he would get up and lock his door before hiding under his bed, curled in a ball as he prayed for someone to save him, like in Anna's story.

His prayers were never answered. If there was a god, he had given up on the Novaks a long time ago.

Castiel didn't pray anymore.

He didn't lock his door anymore, either. When he was twelve, his father had taken off all of the doorknobs from his and his brother's rooms and replaced them. The new ones weren't the kind that were intended for interior doors. Instead of a button lock that could be disengaged with a paperclip, these had actual keys. They were mounted backwards, the keyhole on the inside of the room.

Castiel and his brothers had watched as their father handed the keys to one of his workers and told them to lock them in one of the safes at work. The worker had obeyed. From that day on, the brothers could be locked in their rooms, but they couldn't lock anything out.

Sure enough, it was less than an hour later when Castiel heard the lock engage, his father's heavy footsteps moving on to Raphael's room next door.

Castiel looked up from his book, his gaze traveling out the window as Luc's tail lights wound down the long driveway to the gates of the property.

He tried to remember the end of the story. In a house that sat close by the sea, where the biting winds blew and nipped at the flowers that wouldn't bloom in the poisoned soil…

He couldn't remember the end as Anna told it. Ultimately, though, it didn't matter. Castiel knew the end. He had seen the end. It was only a matter of time.

X

The image of Luc driving away stuck in Castiel's mind all through the weekend. He wasn't allowed to drive; none of the Novak brothers were, technically. Luc had ruined that for them. Because now Luc could drive away whenever he wanted. He could turn his back on the house by the sea, the poisoned dirt kicking up under his tires, and he could run away. Michael couldn't drive. He was two years younger than Luc, three years older than Cas.

Or maybe Michael _could_ drive. Maybe he had learned since he had gone to New York for college. Maybe it was his single act of rebellion against his father. But Castiel doubted it. Michael was too obedient for that. Besides, because Michael was well-behaved, he was allowed to use the car and driver more often. Because Michael wouldn't lie about where he was going. Michael wouldn't turn his back and drive away the way Luc did. Castiel thought that his father would probably let Michael learn to drive if he asked. But Michael wouldn't ask. And Castiel supposed that was sort of the point of the thing.

Raphael and Castiel were the only two of the sons who lived at home. Michael and Luc were both in New York for most of the year, attending Cornell University in Ithaca. It was their father's school, and the patriarch had a lot of eyes out there. That was the only reason he allowed his sons to stray to the opposite coast. Nothing got past him.

Next year, Raphael would be gone as well. It would be another year before Castiel got out, himself. He wasn't looking forward to the long year spent alone. It made him feel a little guilty, but he was relieved when his father's anger was turned against someone other than him.

It was probably a punishment for those feelings that He would be the only one for the anger to be directed at.

When Castiel was little, he had prayed for a sign that under everything, his father loved him. Because despite it all, Castiel did love his father. He would have ripped out his own heart to hear him say just once that he loved him, to receive just one kind look, a single soft word from the man.

That prayer went unanswered, too.

Michael said that their dad loved them; of course he did. "He's just tough, is all. It's to make us strong. The world is a bad place, and he wants us to be ready for it. He wants us to be able to handle it, and to be successful." Michael had smiled when he said that, ruffling Castiel's hair affectionately. "Hang in there, Cassie. You'll see when you're older."

The older Castiel got, the more he doubted that. But sometimes he repeated it to himself, hoping it was true. It made it easier to withstand the harsh lashes of the belt, the sharp sting of the back of his father's hand on his face, the broken sobs from his brothers that seeped through the walls and deep into his bones.

He desperately wanted Michael to be right.

He was terrified that Luc was.

He tried to remember the end of Anna's story.

And in the farthest room of the top floor, there lived the littlest prince. He was imprisoned by a terrible monster, and he hoped that one day someone would rescue him from his prison. But the monster was large and terrible, and all who had tried had failed. Still the prince waited…

He couldn't remember the end. But he had no hope that it was a happy one.


End file.
